Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars.

Org Biomol Chem

Laboratoire d'Innovation Moléculaire et Applications (LIMA), Univ. de Strasbourg | Univ. de Haute-Alsace | CNRS (UMR 7042), Equipe de Synthèse Organique et Molécules Bioactives (SYBIO), ECPM, 25 Rue Becquerel, 67000 Strasbourg, France.

Published: July 2018

We report herein the development of a stereodivergent route towards polyhydroxylated bicyclic azetidine scaffolds, namely 6-azabicyclo[3.2.0]heptane derivatives. The strategy hinges on a common bicyclic β-lactam precursor, which is forged by way of a rare example of a cationic Dieckmann-type reaction, followed by IBX-mediated desaturation. Substrate-controlled diastereoselective oxidations then allow the divergent preparation of novel iminosugar mimics.

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http://dx.doi.org/10.1039/c8ob01065jDOI Listing

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